Boutique Bed and Breakfast near Shelter Island Beaches
Shelter Island is a 27 square-mile beach sanctuary sandwiched between Long Island’s North and South Forks. It’s one of the most low-key spots in the area, marked by uncrowded beaches and quiet summer nights. There’s not a single traffic light on the island and hardly any cars. Residents prefer to travel most places on foot or by bike, and La Petite Maison embraces this leisurely vibe. Guests receive a complimentary bottle of wine upon arrival, and you’re invited to spend your time here relaxing or playing petanque (a French bocce ball-like game) out back.
Housed in a clapboard Victorian home, the inn has five individually decorated guest rooms. The king deluxe unit features a private deck, a jacuzzi tub, and a mini bar stocked with complimentary snacks. The inn’s intimate setup makes it easy to socialize with other guests, or cozy up alone with a bottle of wine. In the morning, head down for a complimentary breakfast of croissants, muffins, and fresh fruit.
La Petite Maison is well placed for exploring the island. Tucked away from the town center, it’s within walking distance of Crescent Beach, a popular swimming spot with dazzling sunset views. You can borrow beach chairs and towels from the front desk, and those who don’t want to walk can hitch a ride on the inn’s complimentary shuttle. The immaculately preserved 19th-century homes of Shelter Island Heights are also nearby.
Long Island’s Shelter Island: Small, Secluded Retreat with Victorian Mansions and Wildlife Preserves
Shelter Island can be reached only by ferry, which keeps the crowds to a minimum, even during the summer. While gourmet restaurants, such as Vine Street Café, draw the occasional celebrity (Kelly Ripa, Anderson Cooper, and Bill Clinton have all been spotted here)—Shelter Island still maintains a relaxed, small-town vibe thanks to its quiet beaches, winding country lanes, and Victorian-era homes. For a private afternoon, find a spot on one of the narrow strips of sand along Oak Tree Lane, which runs parallel to Shelter Island Sound.
The Mashomack Preserve stretches across 2,039 acres, covering a third of the island. Within its varied landscapes—oak woodlands, marshes, and freshwater ponds—you'll find harbor seals, hummingbirds, and one of the largest concentrations of nesting ospreys on the East Coast. At boltax.gallery on North Ferry Road, near the center of the island, you can admire cutting-edge work from such contemporary artists as Melina Berkenwald, whose hand-embroidered photographs resemble Impressionist paintings.